HRID1592464

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID265306

isoquinoline-1-carbaldehyde

C10H7NO

HCID5049666

Sodium triacetoxyborohydride

C6H10BNaO6

结构：Cc1cnc(CNCCCCS(=O)(=O)c2nc3ccccc3[nH]2)c(C)c1

HCID67273026

未命名化合物

PRODUCTS

生成物

结构：Cc1cnc(CN(CCCCS(=O)(=O)c2nc3ccccc3[nH]2)Cc2nccc3ccccc23)c(C)c1

HCID58996979

未命名化合物

收率 50%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

Using General Procedure B: Reaction of [4-(1H-benzoimidazole-2-sulfonyl)-butyl]-(3,5-dimethyl-pyridin-2-ylmethyl)-amine and isoquinoline-1-carbaldehyde in CH2Cl2 with NaBH(OAc)3 gave COMPOUND 177 as a white foam (50% yield). 1H NMR (CDCl3) δ 1.51-1.63 (m, 4H), 2.10 (s, 3H), 2.27 (s, 3H), 2.42-2.45 (m, 2H), 3.26-3.30 (m, 2H), 3.81 (s, 2H), 4.17 (s, 2H), 7.12 (t, 1H, J=8 Hz), 7.27 (s, 1H), 7.37-7.42 (m, 2H), 7.50-7.55 (m, 2H), 7.69-7.74 (m, 3H), 8.05 (d, 1H, J=8 Hz), 8.28 (br s, 1H), 8.40 (d, 1H, J=6 Hz); 13C NMR (CDCl3) δ 17.9, 18.3, 21.4, 23.7, 53.1, 54.4, 57.7, 58.7, 117.2, 120.8, 124.8, 125.9, 126.9, 127.6, 130.2, 132.4, 133.1, 136.3, 139.5, 140.9, 146.2, 148.0, 153.1, 158.2; ES-MS m/z 514 [M+H]+.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-9d24e36b5ff8481d8c2630757cc67f7a
来源数据集: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07291631B2
来源说明: uspto-grants-2007_11

反应 SMILES

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][N:20]=1)(=[O:12])=[O:11].[C:27]1([CH:37]=O)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][N:20]=1)[CH2:37][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1)(=[O:12])=[O:11]